Roommates and Besties Iris Apatow and Olivia Rodrigo Love "Sex and the City" Marathons

Rodrigo and Apatow have never told the story of their first encounter, but their Instagram selfies — which feature tea parties and "Twilight" movie marathons — have left a trail of clues about their friendship. On June 29, 2021, Apatow attended Rodrigo's "Sour" prom while decked out in full "Sour" merch, but the pair were already bonding over their passion for 2000s pop culture — see: their matching "Dump Him" shirts inspired by Britney Spears — and their love for Edward Cullen months before the big night.